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[ CAS No. 1003011-02-6 ] {[proInfo.proName]}

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Chemical Structure| 1003011-02-6
Chemical Structure| 1003011-02-6
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Product Details of [ 1003011-02-6 ]

CAS No. :1003011-02-6 MDL No. :MFCD20702903
Formula : C8H13N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QYQBAJXCDXDNJU-UHFFFAOYSA-N
M.W : 183.21 Pubchem ID :67191677
Synonyms :

Safety of [ 1003011-02-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1003011-02-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1003011-02-6 ]

[ 1003011-02-6 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 1820-80-0 ]
  • [ 24424-99-5 ]
  • [ 863504-84-1 ]
  • [ 1003011-02-6 ]
YieldReaction ConditionsOperation in experiment
1: 57% 2: 17% With triethylamine In 1,4-dioxane at 25℃; for 4h; 2 1H-Pyrazol-3-ylamine (2.00 g, 24.10 mmol) was dissolved in 1,4-dioxane (60 mL), triethylamine (6.77 mL, 48.20 mmol) was added followed by the dropwise addition of di-tert-butyl dicarbonate (5.78 g, 26.50 mmol). The solution was stirred at 25° C. for 4 h. The solution was concentrated in vacuo, diluted with ethyl acetate (100 mL), washed with water (2×50 mL), saturated aqueous brine solution (2×50 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Flash column chromatography (Merck silica gel 60, 40-63 μm, 20% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded both regioisomers 5-amino-pyrazole-1-carboxylic acid tert-butyl ester (less polar product, 2.53 g, 57%) as a white solid; H1-NMR (400 MHz, CDCl3) δ 1.66 (9H, s), 5.10-5.45 (2H, bs), 5.39 (1H, d, J=2.0 Hz), 7.37 (1H, d, J=2.0 Hz); and 3-amino-pyrazole-1-carboxylic acid tert-butyl ester (760 mg, 17%) as a faintly yellow oil; H1-NMR (400 MHz, CDCl3) δ 1.62 (9H, s), 4.00-4.60 (2H, bs), 5.81 (1H, d, J=2.8 Hz), 7.82 (1H, d, J=2.8 Hz).
  • 2
  • [ 1820-80-0 ]
  • [ 24424-99-5 ]
  • [ 1003011-02-6 ]
YieldReaction ConditionsOperation in experiment
57.3% With triethylamine In 1,4-dioxane at 25℃; for 4h; 8 Example 8 (E)-2-(3-Chloro-4-methanesulfonyl-phenyl)-2-isopropoxyimino-N-(1H-pyrazol-3-yl)-acetamide 3-Amino-pyrazole (2 g, 24.1 mmol) was dissolved in 1,4-dioxane (60.25 mL) and triethylamine (6.77 mL, 48.2 mmol) was added followed by the dropwise addition of di-tert-butyl dicarbonate (5.78 g, 26.5 mmol). The solution stirred at 25° C. for 4 h. The mixture was concentrated in vacuo, diluted with ethyl acetate (100 mL), washed with water (2*50 mL), saturated aqueous brine solution (2*50 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Flash column chromatography (Merck silica gel 60, 40-63 μm; 20% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded 5-amino-pyrazole-1-carboxylic acid tert-butyl ester (less polar product, 2.53 g, 57.3%) as a white solid: H1-NMR (400 MHz, CDCl3) δ 1.656 (9H, s, 5.1-5.45 (2H, bs), 5.39 (1H, d, J=2 Hz), 7.37 (1H, d, J=2 Hz).
  • 3
  • [ 1003011-02-6 ]
  • [ 1033780-20-9 ]
  • (E)-5-[2-(3-chloro-4-methanesulfonyl-phenyl)-2-isopropoxyimino-acetylamino]-pyrazole-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% Stage #1: tert-butyl 5-amino-1H-pyrazole-1-carboxylate; (E)-(3-chloro-4-methanesulfonyl-phenyl)-isopropoxyimino-acetic acid With N-ethyl-N,N-diisopropylamine; HATU In acetonitrile at 0℃; for 2h; Stage #2: With sodium hydrogencarbonate In water 8 The estimated 80% pure (E)-(3-chloro-4-methanesulfonyl-phenyl)-isopropoxyimino-acetic acid and (prepared as in Example 6, 99 mg, 0.31 mmol), 5-amino-pyrazole-1-carboxylic acid tert-butyl ester (625 mg, 0.34 mmol) and N,N-diisopropylethylamine (162 μL, 0.93 mmol) were combined in acetonitrile (1.25 mL) and cooled in an ice bath. O-(7-Azabenzotriazole-1-yl)-N,N,N'N'-tetramethyluronium hexafluorophosphate (118 mg, 0.31 mmol) was added and the ice bath was removed. After stirring 2 h, the reaction mixture was evaporated in vacuo. The residue was treated with saturated aqueous sodium bicarbonate solution (1 mL) and extracted with chloroform (2*3 mL). The combined organic phases were dried over sodium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 60% ethyl acetate/hexanes) to afford (E)-5-[2-(3-chloro-4-methanesulfonyl-phenyl)-2-isopropoxyimino-acetylamino]-pyrazole-1-carboxylic acid tert-butyl ester (30 mg, 20%) as a tan solid after lyophilization from aqueous acetonitrile: H1-NMR (400 MHz, CDCl3) δ=1.41 (6H, d, J=6.3 Hz), 1.72 (9H, s), 3.30 (3H, s), 4.66 (1H, m), 6.85 (1H, d, J=1.8 Hz), 7.60 (2H, m), 7.70 (1H, d, J=1.5 Hz), 8.20 (1H, d, J=8.0 Hz), 11.64 (1H, s).
  • 4
  • tert-butyl 5-nitro-1H-pyrazole-1-carboxylate [ No CAS ]
  • [ 1003011-02-6 ]
YieldReaction ConditionsOperation in experiment
With palladium on activated charcoal; hydrogen In methanol at 20℃; 31.b (b) tert-Butyl 5-amino-1 H-pyrazole-1 -carboxylate To a solution of tert-butyl 5-nitro-1 H-pyrazole-1 -carboxylate (1 .9 g) in MeOH (80 ml_) was added Pd/C (500 mg). The reaction mixture was stirred at RT under an atmosphere of hydrogen gas. The reaction mixture was filtered through a bed of Celite and the filtrate was concentrated under reduced pressure to afford the titled compound (1 .7 g), which was used without further purification. LCMS m/z 183.96 (M+H)+.
  • 5
  • [ 24424-99-5 ]
  • [ 1003011-02-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / methanol / 20 °C
  • 6
  • [ 1003011-02-6 ]
  • [ 77718-46-8 ]
  • tert-butyl 5-(3-carbamoyl-4-hydroxyphenylsulfonamido)-1H-pyrazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
750 mg With pyridine at 0 - 20℃; for 16h; Inert atmosphere; 31.c (c) tert-Butyl 5-(3-carbamoyl-4-hydroxyphenylsulfonamido)-1 H-pyrazole-1 - carboxylate To a solution of 3-carbamoyl-4-hydroxybenzene-1 -sulfonyl chloride (lnt-1 , 2.187 g) in pyridine (20 ml_) at 0 °C under nitrogen was added tert-butyl 5-amino-1 H-pyrazole-1 - carboxylate (1 .70 g). The reaction mixture was allowed to warm to RT and stirred for 16 hr. The solvent was removed under reduced pressure and the residue was diluted with water (100 ml_) and extracted with EtOAc (3 x 100 ml_). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product (1 .8 g). The crude product was purified by silica gel column chromatography on a 50 g column eluting with a gradient of 0-2% MeOH/DCM. The desired fractions were concentrated under reduced pressure to afford the titled compound (750 mg). LCMS m/z 383.18 (M+H)+.
  • 7
  • [ 258515-65-0 ]
  • [ 1003011-02-6 ]
  • [ 110-70-3 ]
  • C23H32N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.3% With copper(l) iodide; potassium carbonate In 1,4-dioxane at 100℃; for 12h; 11.1 Step 1 Compound 1a (50.0 g, 160.8 mmol), compound 11a (31.7 g, 160.8 mmol),Cuprous iodide (3.1g, 16.1mmol),N, N’-dimethylethylenediamine (2.8g, 32.2mmol) and potassium carbonate (26.6g, 193.0mmol) were dissolved in dioxane (500ml), warmed to 100 ° C, and incubated for 12 hoursThe reaction was detected by TLC. After the reaction was completed, the temperature was lowered to room temperature. The reaction was quenched by adding 300ml of water, and extracted by adding ethyl acetate (1000mlX2). The organic layers were combined, dried and concentrated. Chromatographic separation gave 57.3g of off-white solidThe off-white solid was compound 11b with a yield of 83.3%.
  • 8
  • [ 1003011-02-6 ]
  • (R)-4-(6-chloro-4-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-methylpyridin-2-yl)-3-methylmorpholine [ No CAS ]
  • C23H32N8O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; Cs2CO3 In 1,4-dioxane at 100℃; Inert atmosphere; 18.4 To a solution of (R) -4- (6-chloro-4- (1, 4-dimethyl-1H-1, 2, 3-triazol-5-yl) -5-methyl pyridin-2-yl) -3-methylmorpholine (100 mg, 0.31 mmol) in Dioxane (2 mL) were added tert-butyl 5-amino-1H-pyrazole-1-carboxylate (85 mg, 0.47 mmol) , Cs2CO3(203 mg, 0.62 mmol) and BrettPhos-Pd-G3 (28 mg, 0.03 mmol) . The mixture was stirred at 100 overnight under nitrogen atmosphere. LC-MS showed the reaction was complete. The mixture was diluted with EA (60 mL) , then washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was dissolved in DCM (5 mL) , then HCl solution (4M in dioxane, 2 mL) was added. The resulting mixture was stirred at room temperature for 12h. LC-MS showed the reaction was complete. The mixture was concentrated under reduced pressure to dryness. The residue was purified by Pre-HPLC (C18, 10-95%, MeOH in H2O with 0.1%HCOOH) to afford the desired product (10 mg, yield: 8.7%) . LC/MS (ESI) : m/z 369 [M+H]+.1HNMR (400 MHz, DMSO) δ 8.13 (s, 1H) , 7.56 (s, 1H) , 6.46 (s, 1H) , 5.97 (s, 1H) , 4.24 -4.14 (m, 1H) , 3.90 (dd, J = 11.2, 3.1 Hz, 1H) , 3.79 (s, 3H) , 3.77 -3.71 (m, 1H) , 3.69 (d, J = 11.5 Hz, 1H) , 3.61 (d, J = 10.8Hz, 1H) , 3.46 (d, J = 2.6 Hz, 1H) , 3.02 (t, J = 12.5 Hz, 1H) , 2.10 (s, 3H) , 1.82 (d, J = 0.8 Hz, 3H) , 1.11 (d, J = 6.6 Hz, 3H) .
  • 9
  • [ 1003011-02-6 ]
  • (R)-4-(6-chloro-4-(3,5-dimethylisoxazol-4-yl)pyridin-2-yl)-3-methylmorpholine [ No CAS ]
  • (R)-4-(3,5-dimethylisoxazol-4-yl)-6-(3-methylmorpholino)-N-(1H-pyrazol-5-yl)pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
11.49% With [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; Cs2CO3 In 1,4-dioxane at 90℃; Inert atmosphere; 20.3 To a (R) -4- (6-chloro-4- (3, 5-dimethylisoxazol-4-yl) pyridin-2-yl) -3-methylmorpholine (150 mg, 0.49 mmol) and tert-butyl 5-amino-1H-pyrazole-1-carboxylate (108 mg, 0.59 mmol) in dioxane (8 mL) were added Cs2CO3(400 mg, 1.23 mmol) and BrettPhos Pd G3 (45 mg, 0.049 mmol) . The mixture was charged with N2twice, then stirred at 90 overnight. The reaction was diluted with water and extracted with EtOAc (30 mL×2) . The combined organic layer was washed with brine (50 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by Pre-TLC (DCM/MeOH=10/1) to afford the desired product (20 mg, yield 11.49 %) . LC/MS (ESI) m/z: 355.0 [M+H]+.[0588]1H NMR (400 MHz, DMSO-d6) δ ppm 12.03 (br s, 1 H) 8.98 (br s, 1 H) 7.55 (br s, 1 H) 6.33 -6.47 (m, 2 H) 5.99 (s, 1 H) 4.30 (br d, J=5.16 Hz, 1 H) 3.94 (br dd, J=11.12, 3.20 Hz, 1 H) 3.84 (br d, J=11.68 Hz, 1 H) 3.71 -3.75 (m, 1 H) 3.61 -3.66 (m, 1 H) 3.45 -3.52 (m, 1 H) 3.03 -3.10 (m, 1 H) 2.44 (s, 3 H) 2.25 (s, 3 H) 1.15 (d, J=6.64 Hz, 3 H) .
  • 10
  • [ 1003011-02-6 ]
  • (R)-4-(6-chloro-4-(1-(methylsulfonyl)cyclopropyl)pyridin-2-yl)-3-methylmorpholine [ No CAS ]
  • tert-butyl (R)-5-((6-(3-methylmorpholino)-4-(1-(methylsulfonyl)cyclopropyl)pyridin-2-yl)amino)-1H-pyrazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; Cs2CO3 In 1,4-dioxane at 100℃; for 4h; Inert atmosphere; 1.6 To a solution of (3R) -4- [6-chloro-4- (1-methanesulfonylcyclopropyl) pyridin-2-yl] -3-methylmorpholine (100 mg, 0.30 mmol) and tert-butyl 5-amino-1H-pyrazole-1-carboxylate (83 mg, 0.45 mmol) in dioxane (10 mL) were added BrettPhos-Pd-G3 catalyst (27 mg, 0.030 mmol) and Cs2CO3(197 mg, 0.060 mmol) . The mixture was charged with N2twice, then stirred at 100 for 4 h. LC-MS showed the reaction was complete. The reaction mixture was diluted with EA (50 mL) , then washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated under vacuo. The residue was purified by flash column chromatography (Silica, 060%ethyl acetate in petroleum ether) to give the title product (59 mg, yield: 41%) . LC-MS (ESI) : m/z 478 [M+H]+.
  • 11
  • [ 1003011-02-6 ]
  • 1-{2-chloro-6-[(3R)-3-methylmorpholin-4-yl]pyridin-4-yl}cyclopentane-1-carbonitrile [ No CAS ]
  • tert-butyl 5-[4-(1-cyanocyclopentyl)-6-[(3R)-3-methylmorpholin-4-yl]pyridin-2-yl]amino}-1H-pyrazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; Cs2CO3 In 1,4-dioxane at 100℃; Inert atmosphere; 31.2 To a solution of 1- {2-chloro-6- [ (3R) -3-methylmorpholin-4-yl] pyridin-4-yl} cyclo pentane-1-carbonitrile (100 mg, 0.33 mmol) and tert-butyl 5-amino-1H-pyrazole-1-carboxylate (90 mg, 0.49 mmol) in dioxane (10 mL) were added BrettPhos-Pd-G3 (29.6 mg, 0.03 mmol) and Cs2CO3(319.6 mg, 0.98 mmol) . The mixture was stirred at 100 overnight under nitrogen atmosphere. LC-MS showed the reaction was complete. The mixture was diluted with EA (50 mL) , then washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (PE : EA = 1: 1, V/V) to give the desired product (104 mg, yield: 70%) . LC/MS ESI (m/z) : 453 [M+H]+.
  • 12
  • [ 1003011-02-6 ]
  • 1-{2-chloro-6-[(3R)-3-methylmorpholin-4-yl]pyridin-4-yl}cyclohexane-1-carbonitrile [ No CAS ]
  • tert-butyl 5-[4-(1-cyanocyclopentyl)-6-[(3R)-3-methylmorpholin-4-yl]pyridin-2-yl]amino}-1H-pyrazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; Cs2CO3 In 1,4-dioxane at 100℃; Inert atmosphere; 32.2 To a solution of 1- {2-chloro-6- [ (3R) -3-methylmorpholin-4-yl] pyridin-4-yl} cyclohexane-1-carbonitrile (100 mg, 0.31 mmol) and tert-butyl 5-amino-1H-pyrazole-1-carboxylate (86 mg, 0.47 mmol) in dioxane (10 mL) were added BrettPhos-Pd-G3 (28 mg, 0.03 mmol) and Cs2CO3(306 mg, 0.94 mmol) . The mixture was stirred at 100 overnight under nitrogen atmosphere. LC-MS showed the reaction was complete. The mixture was diluted with EA (50 mL) , then washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (PE : EA = 1: 1, V/V) to give the desired product (102 mg, yield: 70%) . LC/MS ESI (m/z) : 467 [M+H]+.
  • 13
  • [ 1003011-02-6 ]
  • (R)-4-(6-chloro-4-(1,4-dimethyl-1H-pyrazol-5-yl)pyridin-2-yl)-3-methylmorpholine [ No CAS ]
  • tert-butyl (R)-5-((4-(1,4-dimethyl-1H-pyrazol-5-yl)-6-(3-methylmorpholino)pyridin-2-yl)amino)-1H-pyrazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; Cs2CO3 In 1,4-dioxane 4.3 To a solution of (R) -4- (6-chloro-4- (1, 4-dimethyl-1H-pyrazol-5-yl) pyridin-2-yl) -3-methylmorpholine (120 mg, 0.39 mmol) and tert-butyl 5-amino-1H-pyrazole-1-carboxylate (107.49 mg, 0.587 mmol) in dioxane (10 mL) were added CS2CO3(637.2 mg, 1.96 mmol) and BrettPhos Pd G3 (35.46 mg, 0.04 mmol) . The mixture was charged with N2twice, then stirred at 90 overnight. LC-MS showed the reaction was complete. The reaction was diluted with water (30 mL) and extracted with EA (40 mL×2) . The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under vacuo. The residue was purified by Prep-TLC (PE: EA = 2: 1, V/V) to afford the desired product (80 mg, yield: 45 %) . LC/MS (ESI) m/z: 454 [M+H]+.
  • 14
  • [ 1003011-02-6 ]
  • [ 1233339-68-8 ]
  • tert-butyl (R)-5-((4-(3-methylmorpholino)-6-(1-(methylsulfonyl)cyclopropyl)pyrimidin-2-yl)amino)-1H-pyrazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 6h; Inert atmosphere; 5.6 To a solution of (3R) -4- [2-chloro-6- (1-methanesulfonylcyclopropyl) pyrimidin-4-yl] -3-methylmorpholine (200 mg, 0.60 mmol) and tert-butyl 5-amino-1H-pyrazole-1-carboxylate (166 mg, 0.90 mmol) in Dioxane (10 mL) were added Pd2(dba)3(55 mg, 0.06 mmol) , Xant-Phos (34 mg, 0.06 mmol) and Cs2CO3(394 mg, 1.21 mmol) . The mixture was stirred at 100 for 6 h under N2atmosphere. LC-MS showed the reaction was complete. The reaction mixture was diluted with EA (40 mL) , then washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography on silica gel (PE : EA = 1: 2, V/V) to afford the desired product (129 mg, yield: 44%) . LC/MS (ESI) : m/z 479 [M+H]+.
  • 15
  • [ 1003011-02-6 ]
  • 2-[2-chloro-6-[(3R)-3-methylmorpholin-4-yl]pyrimidin-4-yl]-2-methylpropanenitrile [ No CAS ]
  • (R)-2-methyl-2-(2-((3-methyl-1H-pyrazol-5-yl)amino)-6-(3-methylmorpholino)pyrimidin-4-yl)propanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% Stage #1: tert-butyl 5-amino-1H-pyrazole-1-carboxylate; 2-[2-chloro-6-[(3R)-3-methylmorpholin-4-yl]pyrimidin-4-yl]-2-methylpropanenitrile With [(2-di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate; Cs2CO3 In 1,4-dioxane at 100℃; for 16h; Stage #2: With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 2h; 10.2 To a solution of (R) -2- (2-chloro-6- (3-methylmorpholino) pyrimidin-4-yl) -2-methyl propanenitrile (50 mg, 0.18 mmol) , tert-butyl 5-amino-3-methyl-1H-pyrazole-1-carboxylate (70 mg, 0.36 mmol) and Cs2CO3(174 mg, 0.53 mmol) in Dioxane (5 mL) was added BrettPhos Pd G3 (16 mg, 0.018 mmol) . The mixture was stirred at 100 for 16 h. LC-MS showed the reaction was complete. The reaction mixture was diluted with EA (40 mL) , then washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated under vacuo. The residue was dissolved in DCM (4 mL) , then HCl solution (4M in dioxane, 2 mL) was added. The mixture was stirred at room temperature for 2h. LC-MS showed the reaction was complete. The reaction mixture was concentrated under vacuo. The residue was purified by Prep-HPLC (C18, 10-95%, MeOH in H2O with 0.1%HCOOH) to give the desired product (8 mg, yield: 13%) . LC/MS (ESI) : m/z 342 [M+H]+.1H NMR (400 MHz, DMSO) δ 11.78 (s, 1H) , 9.07 (s, 1H) , 6.26 (d, J = 17.8 Hz, 2H) , 4.40 (dd, J = 13.5, 7.2 Hz, 1H) , 4.01 (d, J = 13.2 Hz, 1H) , 3.93 (dd, J = 11.3, 3.3 Hz, 1H) , 3.72 (d, J = 11.4 Hz, 1H) , 3.58 (dd, J = 11.4, 2.9 Hz, 1H) , 3.45 -3.42 (m, 1H) , 3.17 -3.10 (m, 1H) , 2.17 (s, 3H) , 1.64 (s, 6H) , 1.19 (d, J = 6.7 Hz, 3H) .
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